5-Hydroxy-8-[2-hydroxy-5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl]-2-(4-hydroxyphenyl)-7-methoxychromen-4-one

Details

• Internal ID: 201aaa0a-eb09-4e24-a53b-bf71adcd805b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 5-hydroxy-8-[2-hydroxy-5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenyl]-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3)O)C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)OC)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3)O)C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)OC)O
• InChI: InChI=1S/C32H22O10/c1-39-18-10-21(35)30-22(36)12-26(41-28(30)11-18)16-5-8-20(34)19(9-16)29-27(40-2)14-24(38)31-23(37)13-25(42-32(29)31)15-3-6-17(33)7-4-15/h3-14,33-35,38H,1-2H3
• InChI Key: SVIMIMQAVRQGEK-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₂₂O₁₀
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.12129689 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.74
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9672	96.72%
Caco-2	-	0.8377	83.77%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8928	89.28%
OATP2B1 inhibitior	-	0.5658	56.58%
OATP1B1 inhibitior	-	0.3212	32.12%
OATP1B3 inhibitior	+	0.9770	97.70%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9093	90.93%
P-glycoprotein inhibitior	+	0.8156	81.56%
P-glycoprotein substrate	-	0.6453	64.53%
CYP3A4 substrate	+	0.6198	61.98%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.7247	72.47%
CYP2C9 inhibition	+	0.7879	78.79%
CYP2C19 inhibition	+	0.6463	64.63%
CYP2D6 inhibition	-	0.7929	79.29%
CYP1A2 inhibition	+	0.6457	64.57%
CYP2C8 inhibition	+	0.8873	88.73%
CYP inhibitory promiscuity	+	0.5684	56.84%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.6106	61.06%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.8505	85.05%
Skin irritation	-	0.7338	73.38%
Skin corrosion	-	0.9599	95.99%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6452	64.52%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9601	96.01%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5663	56.63%
Acute Oral Toxicity (c)	III	0.6241	62.41%
Estrogen receptor binding	+	0.8948	89.48%
Androgen receptor binding	+	0.9464	94.64%
Thyroid receptor binding	+	0.6386	63.86%
Glucocorticoid receptor binding	+	0.8181	81.81%
Aromatase binding	+	0.5522	55.22%
PPAR gamma	+	0.6957	69.57%
Honey bee toxicity	-	0.7464	74.64%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5449	54.49%
Fish aquatic toxicity	+	0.9256	92.56%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4822	P56817	Beta-secretase 1	6250 nM	IC50	PMID: 20598535

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL242	Q92731	Estrogen receptor beta	98.52%	98.35%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	98.08%	99.15%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.67%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.06%	94.00%
CHEMBL3194	P02766	Transthyretin	95.77%	90.71%
CHEMBL2581	P07339	Cathepsin D	95.43%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.56%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.17%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.14%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.26%	86.33%
CHEMBL1907	P15144	Aminopeptidase N	87.70%	93.31%
CHEMBL4208	P20618	Proteasome component C5	87.07%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.95%	96.21%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.13%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.83%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.79%	91.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.73%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.05%	86.92%
CHEMBL2535	P11166	Glucose transporter	83.99%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.62%	99.23%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.11%	97.28%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.98%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.88%	95.50%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	81.83%	89.23%
CHEMBL3401	O75469	Pregnane X receptor	80.86%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.25%	93.65%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.02%	95.89%

Plants that contains it

• Amentotaxus yunnanensis
• Retrophyllum rospigliosii
• Taiwania cryptomerioides

Cross-Links

• PubChem: 13871759
• NPASS: NPC100049
• ChEMBL: CHEMBL1208793
• LOTUS: LTS0016867
• wikiData: Q105262060